Weird Celebrity Couples You Forgot Dated in the ‘90s and the ‘00s

Hands up if you forgot Ryan Reynolds and Alanis Morissette were a couple!

Weird celebrity couples from the past may come and go, and we may even forget about their odd pairings – but we still have pictures. You can’t hide from us. Take a look at the weird celebrity couples you forgot dated in the ‘90s and ‘00s, some of them will blow your mind…

Sandra Bullock and Matthew McConaughey

Aw, weren’t these two the cutest? These two met on the set of A Time To Kill in 1996, and started dating pretty soon after. But it didn’t seem to materialize into anything special, as a year later she reported that he was a ‘powerful force’ in her life and that they had ‘fabulous chemistry together, but it never really amounted to anything else.

Madonna and Dennis Rodman

Remember the time when Madonna dated a basketball player? No, neither do we. But it happened. The two were dating in 1994 and dated for a couple of months – and it seems the pop superstar loved a basketball player. She even once called him ‘the Madonna of the NBA world.’ Right. However, it only really seemed to be a fling. Slam-dunk.

Gwyneth Paltrow and Brad Pitt

These two blondies hit it off in the ‘90s – and shared everything. Probably even their hair dye. The two of them got together in 1995, and even got engaged! The engagement got called off in 1997 though, and the two separated – leading the way towards Brangelina, the ultimate couple goals.

Julia Roberts and Kiefer Sutherland

Julia Roberts and Kiefer Sutherland dated when Julia was at the peak of her Hollywood presence and fame (which to be honest, never seemed to end). The two of them dated in the ‘90s and were even engaged. But a few days before her wedding, she was a literal Runaway Bride and ran off with Sutherland’s friend, Jason Patric. That had to hurt.

Winona Ryder and Matt Damon

We’re so sad this relationship didn’t pan out. The two famous stars of Hollywood began dating each other after they were introduced to each other by Gwyneth Paltrow (it’s a small world when you’re rich and famous) and hit it off straight away. The two only really dated for a year, which is a shame, because they would have made the most beautiful babies.

Ashton Kutcher and Brittany Murphy

Ashton Kutcher and Brittany Murphy’s relationship was a match made in Hollywood. Quite literally. The two of them met on the set of Just Married in 2003 where they played a married couple, and they got close in real life. So close, in fact, that there were rumors they were even engaged offset. But sadly, their relationship only lasted a couple of months.

Cameron Diaz and Matt Dillon

You probably remember Cameron Diaz and Matt Dillon from the hilariously funny movie, There’s Something About Mary. Sure, Dillon plays a stalker, but who cares? At the time of filming, the two were actually dating and had been for three years. Although they ended things just after they called wraps on the movies filming.

Matthew McConaughey and Janet Jackson

Would you ever believe these two were actually an item? The king of Hollywood and the Queen of pop? Quite possibly the oddest combination of people ever. But it happened. They dated for a few months in 2002, but it seems it didn’t last too long. Sorry Ms. Jackson, oooh, this love isn’t for reaaaaaaaal

Courtney Love and Ed Norton

And the award for the most random relationship in the history of celeb couples goes to….Courtney Love and Ed Norton. The pair started dating in 1996 after appearing in The People vs. Larry Flynt and hit it off so much they even got engaged! They were engaged for six months and together for three years before they eventually broke up in 1999. Weird.

Julia Roberts and Benjamin Bratt

Because we love Julia Roberts so much, we had to write about her twice. And also because she had a taste in men that proved to be a weird pairing. Although these two looked like a picture postcard, their work schedules made their four-year relationship a strain, and they eventually parted ways.

Ellen DeGeneres and Anne Heche

If you don’t remember these two together, simply Google ‘Ellen DeGeneres and Anne Heche + Red Carpet’ and we’re sure the memories will come flooding back. These two rocked the red carpet and coordinated their outfits, their eyewear, and their hair. Genius. This relationship is even more memorable because this was Ellen’s first same-gender relationship since she publicly came out in 1997.

Lance Armstrong and Ashley Olsen

Okay, we really really really wish we remember this happening – because it sounds like we may have been having a nightmare. Professional cyclist Lance Armstrong dated former child-star and one-half of the Olsen sisters, Ashley Olsen back in 2007 just after he’d split from Tory Burch. But it didn’t last long, and Lance was urged to ditch Ashley to protect his image as fans weren’t happy out their 15-year age gap.

January Jones and Ashton Kutcher

January Jones and Ashton Kutcher dated from 1998 until 2001 when she was an Abercrombie and Fitch model trying to make it in the acting world. But it seems their relationship was cut short because Ashton had no faith in her acting and told her she wasn’t going to make it in Hollywood. Well, she sure showed him.

Alyssa Milano and David Arquette

Alyssa Milano and David Arquette had a brief fling in 1991, but it ended pretty quickly. The Who’s The Boss? Star and the Scream star had pretty hectic schedules and they both had their eyes on other people…

Minnie Driver and Matt Damon

Weren’t these two just the cutest? Their relationship didn’t start on the school playground. Instead, their love blossomed on the set of Good Will Hunting. They first started dating in 1996 and dated for a year before Matt Damon did the unthinkable. Without talking to his ‘girlfriend’ or ending things in person, he went on Oprah and announced it to the world. Not cool, Matt Damon.

Ryan Gosling and Sandra Bullock

Okay, how did we ever forget that these two were a couple?! These two are the greatest. But their relationship was pretty weird. Sandra and Ryan dated back in the early ‘00s and get this – he was 21, and she was 37. Who knew Sandra was a cougar? Despite the fact they look amazing together, their relationship eventually ended, and Ryan went on to have major #RelationshipGoals with Eva Mendes.

Courteney Cox and Michael Keaton

Friends actress and the actor known for The Mary Tyler Moore Hour started dating in 1990 and lasted for five years! Friends close to the pair often said that the spark between them was undeniable, but the relationship broke down after Courteney was linked with fellow Friends star, Matthew Perry.

Mariah Carey and Derek Jeter

It’s hard to think of Mariah Carey with someone other than Nick Cannon – but it happened. Mariah hooked up with Yankee star, Derek Jeter in 1996 and dated for nearly two years. In the end, the two found the media pressure surrounding their relationship too much, and decided to part ways but still stayed friends.

Sarah Jessica Parker and Robert Downey Jr.

What do you get if you mix a Sex and the City star with Iron Man? Well, Sarah Jessica Parker and Robert Downey Jr.’s relationship. The two of them dated back in the early ‘90s but sadly broke up because of Robert’s notorious drug problem. Which, in hindsight, is probably for the best, who would want to see Iron Man going shopping? Not us.

John Mayer and Taylor Swift

John Mayer were the sweethearts of the late ‘00s. We could just imagine them having romantic dinner together, singing country songs and serenading each other. I mean, that’s what singers do all the time, right? But sadly, these lovebirds’ schedules kept them apart, and they ended their relationship in 2010. But it didn’t end well, with Mayer since cursing the day she was born. Right…

Madonna and Vanilla Ice

Okay, how did we not remember this happened?! Ice Ice, Baby. Back in 1990, these two dated in the only way Madonna and Vanilla Ice could. Their relationship was fuelled by substances, alcohol, partying and (ahem) physical encounters. But their relationship came to an end after Madonna published her book which held grown up (cough) pictures of Ice in it.

Rachel Wood and Marilyn Manson

We have to give credit to anyone who decides to date, Marilyn Manson. We’re sure he’s a great guy, but we just couldn’t risk him stealing our eyeliner all the time. But Rachel Wood and Marilyn Manson had a pretty solid relationship in Hollywood terms. They dated and were engaged for three years!

Quentin Tarantino and Margaret Cho

It’s hard to think of hard-nosed Tarantino with a hilarious comedienne – but anything seemed to happen in the ‘90s. These two met after Quentin was roped in to direct an episode of ‘All American Girl’ – Cho’s show. They hit it off from there but broke things off after a couple of months.

Whoopi Goldberg and Ted Danson

If you don’t remember Whoopi Goldberg as part of this couple, you might remember the scandal surrounding Ted Danson. Ted and Whoopi started having an affair while he was still married with his wife and came into the public eye when he suffered from a pretty public $30 million divorce. They eventually carried on their relationship…until they split up in 1993, just one year after the divorce proceedings.

Cindy Crawford and Richard Gere

Okay, so you probably remember this one, right? Richard Gere and Cindy Crawford’s relationship was no stranger to people sticking their ear in. Many people thought their 17-year age gap was pretty weird, but they took no notice and started dating in the late ‘80s and were married for four years before they eventually split – although Cindy did report they did break up because of the age gap. Oops.

Tom Cruise and Sofia Vergara

We could seriously get behind this coupling. I mean, it’s Tom Cruise for one. And secondly, it’s Sofia Vergara. Some of the most beautiful people in Hollywood. A match made in heaven? The pair briefly dated back in 2005, and Tom Cruise was all for it. But in the end, Cruise’s allegiance and beliefs about Scientology was ultimately a deal breaker, and she broke things off with him. Shame.

Wilmer Valderrama and Lindsay Lohan

When two child stars come together – you just know there will be trouble. But for a while, these two were the best pairing, and they just looked SO GOOD together. Nevertheless, we all know what went on with Lindsay Lohan. We still love Wilmer Valderrama though, even though we still want to call him Fez…

Kim Kardashian and Nick Cannon

Kim Kardashian is known for her lovers (and her marriage that lasted only 72 days), but one relationship you probably don’t remember is when she dated Nick Cannon. And we hate to say it, but we really liked them together. But sadly, they only dated for a couple of months, and Nick moved on to Mariah Carey.

Ryan Reynolds and Alanis Morissette

Isn’t it ironic? Well, it’s not really, as these two were actually a pretty cute couple. The singer and actor first met at Drew Barrymore’s party back in 2002, dated for two years and then got engaged! And they seemed so in love for so many years, but they never made it down the aisle and split up in 2007.

Rihanna and Shia LaBeouf

So we have a feeling that if these two were still together, everything would be right in the world and that we’d have world peace. Just a hunch. These two dated back in the ‘00s but it didn’t really amount to anything, with Shia reporting that ‘the spark wasn’t there. We weren’t passionate about each other in that way, so we remain friends.’ Shame.